Songs you buy on the I Store (Songs from ITunes) are downloaded in a format calledAAC(Advance audio coding); the Windows Media Player doesn't recognize this file format.
When you click on the library tab (on windows media player) and then add to library, Windows Media Player will search for available files, it will find your songs bought on the iTunes store but it won’t import them, you will have toconvert them to a format that the player canunderstand.
Follow these steps and check if it helps:
1. Open up iTunes, click on Edit, Preferences, Advanced and Importing.
2. Change your "Import Using" drop-down to "MP3 Encoder".
3. Exit from your preferences and go to the main library view in iTunes. You may want to sort all of your music by "File Type".
4. Highlight all of your unprotected AAC files. (You can not convert or play songs you purchased from the iTunes Music Store because of a lock Apple is forced to put on the files called "FairPlay".)
5. Right-click and select "Convert Selection to MP3". It'll take awhile.
6. When all the files have converted to MP3 format, close iTunes.
7. Open Windows media player, hit F3.
8. You get an "add to library" drop down box with a list of folders that WMP is monitoring for new media files. If you don't see this list, click on "advanced Options" then click on ADD Navigate to the root folder holding your iTunes music files. This path will usually be c:\My Documents\My music\itunes\itunes music.
9. Click OK. WMP will scan the folder and all its subfolders and add those music files to your library. Any AAC files and music purchased from the iTunes Music Store will be skipped.
10. When the import is finished exit WMP and open Music Bridge From the "Synch from iTunes" box chose "All Data" confirm this when asked: Do you really want to.
11. Wait till your data is synced
12. When this is done open WMP and check to see that the files are indeed there.
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